Diels-Alder Cycloadditions of Masked o-Benzoquinones with Alkenes. 2015

Effie Georgopanou, and Katerina-Irene Martini, and Panagiotis Pantazis, and Paulos Pelagias, and Penelope Voulgari, and Lazaros P Hadjiarapoglou
Department of Chemistry, University of Ioannina , GR-45110 Ioannina, Greece.

Diels-Alder cycloadditions of 3-oxobut-1-enyl substituted orthoquinone monoketals with olefinic dienophiles furnished functionalized ortho-endo bicyclo[2.2.2]octenone derivatives with high regio- and stereoselectivities. The competition between self-dimerization and Diels-Alder cycloaddition with an external dienophile usually exists, except in the case of 5-substituted orthoquinone monoketal.

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